Sulfuric Acid → HCID 69235813, compound

Temperature

0 °C

To a 250 mL flask were added CTABr (0.933 g, 2.56 mmol), NaOH (23.04 g, 576 mmol), and H2O (100 mL), and the resulting solution was warmed to 50° C. (6aR,10aS)-2-fluoro-9-methoxy-6a-nitro-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-6-one (3.75 g, 12.80 mmol) was rapidly added to the alkaline solution and left under stirring for 1 h. The green solution was then cooled to 0° C., and added dropwise to a solution of H2SO4 (3.75 M, 100 mL) also cooled to 0° C. The mixture was left stirring at 0° C. for 5 min, and was then allowed to stir at RT for 1 h. The mixture was then saturated with brine, and extracted with EtOAc. The organic layer was then dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by flash chromatography on silica gel afforded the product as a white solid (0.50 g, 19%); MS (EI) m/z=204 [M+].

1. additionwas rapidly added to the alkaline solution
2. waitleft
3. temperaturealso cooled to 0° C
4. waitThe mixture was left
5. stirringstirring at 0° C. for 5 min
6. stirringto stir at RT for 1 h
7. extractionsaturated with brine, and extracted with EtOAc
8. dry with materialThe organic layer was then dried over anhydrous Na2SO4
9. concentrationconcentrated under reduced pressure
10. customPurification by flash chromatography on silica gel

ORD record

ord-36387b075bbe4559aef6d9388caeb155

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07297704B2